Miles (Paul Giamatti) and Jack (Thomas Haden Church) may be the two most mismatched drinking buddies on film. Touring California wine country for a few days before Jack’s impending marriage, Miles is a grape snob (he famously refuses to drink any “f—ing Merlot”) who really does want to enjoy the various vintages of the local vineyards, while Jack is just along for the ride, aiming for a last fling or two before submitting to the shackles of matrimony. They have little in common except a shared history, a penchant for thinking with the wrong organ, and a desire to dull the pain of personal failure through overindulgence.
As Miles blows it with a lovely fellow wine enthusiast, Maya (Virginia Madsen), and as Jack allows his libido to get him into increasingly serious trouble, Miles’ lofty pretensions are deflated, and he realizes that any wine, even Merlot, is good enough to get you loaded. (He also engages in one of the most hilarious/pathetic drunk-dialing-your-ex scenes in movies.)
At least he learns from Jack that he can man up, and from Maya that redemption is possible. Alexander Payne’s adaptation of Rex Pickett’s novel is billed as a comedy, and it has plenty of laugh-while-you-cringe moments, but it can also be as bitter as the dregs of an old bottle whose once-sweet nectar has turned to vinegar.